quinupristin

Also known as RP-57669

Quinupristin is a streptogramin B antibiotic, used in combination with dalfopristin under the trade name Synercid. It has activity against Gram-positive and atypical bacteria but not Gram-negative bacteria. It inhibits bacterial protein synthesis. The combination of quinupristin and dalfopristin is not active against Enterococcus faecalis and needs to be given in combination with other antibacterials for mixed infections that involve Gram-negative organisms. Category:Antibiotics

Chemical data

Formula: C53H67N9O10S
Molecular weight: 1022.2 g/mol
IUPAC name: N-[(3S,6S,12R,15S,16R,19S,22S,25R)-25-[[(3S)-1-azabicyclo[2.2.2]octan-3-yl]sulfanylmethyl]-3-[[4-(dimethylamino)phenyl]methyl]-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentazatricyclo[20.4.0.06,10]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide
SMILES: CC[C@@H]1C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)N3C[C@H](C(=O)C[C@H]3C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CS[C@@H]6CN7CCC6CC7)CC8=CC=C(C=C8)N(C)C)C
InChIKey: WTHRRGMBUAHGNI-LCYNINFDSA-N
XLogP: 4.2
Polar surface area: 257 Å²
H-bond donors: 4
H-bond acceptors: 14
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1999
Admin. routes: parenteral
Indications: osteomyelitis

via ChEMBL · EBI

Research

1,312 papers

Quinupristin-Dalfopristin.2012
Quinupristin-dalfopristin.Drugs · 1996
Quinupristin/dalfopristin.Expert opinion on pharmacotherapy · 2002
Quinupristin-dalfopristin: an overview.Pharmacotherapy · 2000
[Quinupristin/dalfopristin].Revista de medicina de la Universidad de Navarra · 2001

via PubMed

Wikidata facts

Subclass of: streptogramins
Mass: 1021.473
Has use: medication

Show 5 more facts

chemical formula: C₅₃H₆₇N₉O₁₀S
isomeric SMILES: CC[C@@H]1C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)N3C[C@H](C(=O)C[C@H]3C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CS[C@@H]6CN7CCC6CC7)CC8=CC=C(C=C8)N(C)C)C
canonical SMILES: CCC1C(=O)N2CCCC2C(=O)N(C(C(=O)N3CC(C(=O)CC3C(=O)NC(C(=O)OC(C(C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CSC6CN7CCC6CC7)CC8=CC=C(C=C8)N(C)C)C
medical condition treated: staphylococcal infection
subject has role: antibiotic

Sources (2)

via Wikidata · CC0

~2 min read

Encyclopedic overview

1 sections

Contents

References

{{Drugbox | IUPAC_name = N-{(6R,9S,10R,13S,15aS,18R,22S,24aS)-18- {[(3S)-1-azabicyclo[2.2.2]oct-3-ylthio]methyl}-22-[4-(dimethylamino)benzyl]- 6-ethyl-10,23-dimethyl-5,8,12,15,17,21,24-heptaoxo-13-phenyldocosahydro-12H- pyrido[2,1-f]pyrrolo-[2,1-l][1,4,7,10,13,16] oxapentaazacyclononadecin-9-yl}-3- hydroxypyridine-2-carboxamide | image = Quinupristin.png | image_class = skin-invert-image | CAS_number = 120138-50-3 | UNII_Ref = | UNII = 23OW28RS7P | ATC_prefix = | ATC_suffix = | PubChem = 5388937 | DrugBank = | ChEMBL = 1200649 | ChemSpiderID = 4470884 | smiles = CC[C@@H]1C(=O)N2CCC[C@H]2C(=O)N([C@H](C(=O)N3C[C@H](C(=O)C[C@H]3C(=O)N[C@H](C(=O)O[C@@H]([C@@H](C(=O)N1)NC(=O)C4=C(C=CC=N4)O)C)C5=CC=CC=C5)CS[C@@H]6CN7CCC6CC7)CC8=CC=C(C=C8)N(C)C)C | StdInChI = 1S/C53H67N9O10S/c1-6-37-50(68)61-23-11-14-38(61)51(69)59(5)40(26-32-16-18-36(19-17-32)58(3)4)52(70)62-28-35(30-73-43-29-60-24-20-33(43)21-25-60)42(64)27-39(62)47(65)57-45(34-12-8-7-9-13-34)53(71)72-31(2)44(48(66)55-37)56-49(67)46-41(63)15-10-22-54-46/h7-10,12-13,15-19,22,31,33,35,37-40,43-45,63H,6,11,14,20-21,23-30H2,1-5H3,(H,55,66)(H,56,67)(H,57,65)/t31-,35+,37-,38+,39+,40+,43-,44+,45+/m1/s1 | StdInChIKey = WTHRRGMBUAHGNI-LCYNINFDSA-N | C=53|H=67|N=9|O=10|S=1 | bioavailability = | protein_bound = | metabolism = | elimination_half-life = 3.1 hours | excretion = | pregnancy_AU = | pregnancy_US = | pregnancy_category= | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = }}

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